My wife and I recently split up and it was a very hostile situation. She was very bitter about just about everything. Our lack of money, our lack of sex, and we both had basically had enough. It didn’t help that some of her clothes would go missing. I couldn’t help it – they just seemed to look better on me. We tried staying under the same roof until we could finalize a divorce, but that just wasn’t going to happen. So we separated. She stayed at the house and I moved into an apartment on the other side of town.
After I moved in, I found such a great sense of relief that I became excited about the future. While she knew I was a crossdresser, she never wanted to participate. I never really wanted that either – for the most part, it was just a private thing I did when I was alone and needed some space. I was always straight and sex was not the reason I would dress, but things were different now. I found myself free to do what I wanted and explore other aspects of my life.
So I started by going shopping; online shopping at least. I spent a bunch of money on clothes, shoes, lingerie makeup and wigs. And because I was in a rush I spent about the same amount of money in overnight shipping.
I was so excited when everything arrived that morning. I tore through the boxes and started putting the outfits together on the bed. Like every woman – changing my mind over and over again. I started with the lingerie. I had several sets in the new wardrobe collection, but one stood out to me. It was a black lace bra and matching panties. As I put on each piece I would go to the mirror and admire myself. You see I was very passable when I tried to be. I had always been cautious because I didn’t want it to be too obvious, but when fully transformed I was a beautiful woman.
After the lingerie, I slipped on a pair of black tights that firmly caressed my legs. Then came the dress. I picked out a stunning black skirt and white top that really looked slimming and accentuated my hips.
I tried the wigs but they just didn’t look realistic enough for me – so, I decided to just style my real hair and use some hair extensions instead. Then I moved to the make-up, which I had really mastered over the years. I kept it subtle around my cheeks and eyes, but went with a deep red lipstick, to add some “sexy” to my look.
Now that the transformation was completed, I slipped on a pair of black pumps and paraded around the apartment. Posing in front of the mirror and taking pictures in provocative poses, I was really excited at the opportunity to be “me”. As the day turned into the evening I was still dressed and wanted more. Most of the day I toyed with the idea of venturing out, which I had never done before.
Now that things had changed, it was time for me to try new things, so I changed into a black cocktail dress, waited for the sun to go down and went to a local gay bar. If it had been a regular bar I wouldn’t know how I would be received. I was there for about an hour and while I was excited about being out in public, it wasn’t exactly what I was hoping for. I decided I would call it a night. I had already done more than I had in the past, so I figured the next step could come on another night.
As I walked to my car, I looked across the street and saw a busy restaurant. I wasn’t planning on going, but I was already dressed and took one chance of going out. Why not take another and go to a new place.
When I walked in, the waitress looked at me and asked me if I was meeting with someone since it was rare for a woman to come in by herself. I told her that I was meeting someone and they were running late, so I was shown to a table and ordered a glass of wine.
I wasn’t sure how long I would stay. Not sure if anyone would recognize me or figure out I was a man. So I spent most of the time scanning the bar and occasionally looking up towards the front door to see how busy it was getting. Then something happened I never expected.
As I turned back around from checking the front door, the waitress brought me another glass of wine – which I didn’t order.
“Did I order this?” I asked.
“This is compliments of the gentleman at the bar.” The waitress replied.
The waitress pointed me to the end of the bar were a young gentleman was sitting. I wasn’t sure how to react, but he gave me a quick smile and raised his glass. I politely smiled and gestured to him to join me.
As he walked over to me I caught myself giving him the once over as if I was admiring a piece of meat. He was wearing tight jeans and a white t-shirt and brown sports coat.
“Hi, I’m Sam.” he said.
I looked at him with a completely blank stare. Not because I was shocked that he was interested, but the one thing I forgot was my girly name.
“Uh… hello?” He asked as he tried to gather my attention.
“Oh… I am sorry… Alex.” I said nervously.
As he sat down, he said, “Sorry about that. I didn’t mean to catch you off guard.”
“No. It’s okay, I just had a bunch of stuff in my head.” I replied. “Thanks for the drink.”
We continued to talk for a while and I really started to enjoy the attention, but I knew it couldn’t last all night. Sam and the alcohol had other ideas. He kept buying drinks and I kept putting them away. Eventually, I was way too drunk to drive. Sam offered me a ride home, but I decided to take a cab instead. As we walked out of the bar after last call, he had his arm around me practically, holding me up. While we waited together for the cab to arrive, Sam moved into kiss me, but I pulled away quickly.
“Sorry about that,” Sam said.
“It’s okay Sam, “ I replied and gave in, moved in and kissed him instead.
It was the first time I had kissed a guy before. While it felt a little unusual because of the rough skin, Sam was very smooth and didn’t push too hard – he let me be in control. As we kissed I found my hand sliding down his back to his waist and his hand slowly slid from my waist to my hips.
When the cab arrived and honked the horn, it startled both of us and we both laughed about it as he helped me into the cab. Before I left, he handed me his phone number and I told him I would call him and we could get together again.
When I got back to the apartment, I was really excited. My first night out and I pulled it off and landed a date at the same time. I did have to come back to reality. I knew that I couldn’t get serious with a straight guy. It could be disastrous for both of us. So I just laid in bed still dressed and enjoyed the memory of the night.
The next day, I couldn’t stop thinking about the night before. Sam was fantastic and I wanted to continue things even in a platonic way, but I didn’t want to lead him on. I decided to call him that afternoon.
“This is Sam,” he said.
“Hey Sam, it’s Alex. Remember me?” I said.
“Are you kidding, you are all I have thought about all day today,” Sam said excitedly.
“Come on, Sam.” I said, “I am sure you had other things to think about today.”
“Not really.” He replied, “I am really glad you called. To be honest I didn’t think you would.”
“Well, to be honest, I wasn’t sure I would either, “ I said, “So I am taking a chance…. What are you doing tonight?”
“Nothing actually,” Sam said.
“Would you like to have dinner?” I said.
“Sure, is there any place you want to go?” Sam asked.
“I was thinking of maybe having dinner at my place. I can text you my address.” I said.
“Even better. What time?” Sam asked.
“Say about 8 o’clock,” I said.
“Perfect, I can’t wait,” Sam said.
“Now I am not the greatest cook so no expectations,” I said.
“No problem,” Sam said.
“Okay then, I guess I will see you tonight,” I said.
“Thanks, Alex. See you tonight,” Sam said.
Now the date was set… but the now to the hard part, dinner and still hiding my true self. I am sure he will try and I may let him try, but I guess I just need to know how far this can really go.
I decided to wear a nice red dress with tan nylons attached to the garters on the red bustier, matching panties and leopard print pumps. I got dressed while dinner was in the oven. Just about the time dinner was ready, so was I, and I was really getting excited. The doorbell rang and it was Sam holding a bottle of wine. He obviously remembered.
We sat and had dinner and talked about ourselves some more and of course I had to fudge a little bit about myself since he didn’t know my true identity. After dinner, we decided to watch a movie and sat on the couch together. It wasn’t long before he began kissing me and this time I didn’t stop him. He began caressing my thighs and working to my firm ass. I had a hold of his face and slowly worked my hands down his shoulders to his back. I felt his hand start to move to my inner thigh and I had to stop him before he found the shock of his life.
“Are you okay,” Sam asked.
“Not really.” I said, “ I don’t want to hurt you.”
“Don’t worry, it’s okay,” Sam said.
“I have to worry. You don’t understand.” I said.
“Understand what?” Sam asked.
“If I tell you, I want you to understand that I didn’t mean for any of this to happen. I really like you.” I said.
“I like you too,” Sam replied.
“You might not think so when I tell you what I have to say,” I said.
“Listen… you tell me and if there’s a problem we will work it out together,” Sam said.
“Okay, promise me that when I tell you – if you can’t handle it you will just leave and never come back,” I said.
“That is not going to happen,” Sam said.
“Promise me.” I requested.
“Okay, I promise.” Sam agreed.
I got up with tears in my eyes and very nervously looked at him.
“I am really a man,” I said as I prepared for the worst.
Sam was very quiet, then got up from the couch and walked over to me and put his hands on my shoulders.
“I know.” He said.
“You do?” I asked in amazement.
“I spotted you at the bar and followed you to the restaurant.” He explained.
“I’m not sure what to say.” I said, “It was the first time I had ever gone out… and I never thought any of this would happen.”
“But… you did want it to happen.” He replied.
“Maybe, I guess I just never thought I would ever have anyone accept me for all of this.” I said as I gestured at my transformation.
“You think I care about that?” Sam asked.
I looked up at him and he had a determined look on his face and leaned in and kissed me passionately. I pulled away and looked at him for a quick second, then wrapped my arms around him and continued kissing him. He then picked me up and took me into the bedroom. He placed me on the bed and began taking his clothes off.
“I have never done this before,” I said.
“That’s okay, trust me,” Sam said.
I think we were both too excited to care so we just threw caution to the wind. He got down to his black boxer briefs and I down to the red lingerie. I wasn’t sure what to do so I just decided to take charge and make sure he left as happy as he made me.
I began kissing his smooth chest and stomach while rubbing his crotch and the huge stiff bulge showing through his underwear. When I got to his waistband I slowly pulled his underwear down, exposing his cock. I moved down and began licking it while trying to look up at him.
I dropped to my knees as my arms wrapped around his legs and my hands on his firm ass, I continued to wet his cock with my tongue, and then quickly wrapped my red lips around his shaft and began sucking. I felt his knees buckle so I slowly sat him down and pushed him onto his back. I stayed crouched between his legs and grabbed a hold of his cock firmly and continued to mouth fuck him.
He continued repeating over and over, “Oh my god. That feels great.”
“Do you like that?” I asked.
“Oh yes,” he said as he put his hand on the back of my head, “It feels great.”
I kept going until he pulled my hair back pulling my mouth off his cock and sat up. He stood up and helped me to my feet. He gently kissed me and then put his hand on my bulging cock.
“You don’t have to Sam,” I said.
“I know, but I want you to experience what it feels like to be with a man.” He said.
I wasn’t sure what he meant at first, but when he positioned me on the bed and on my stomach I couldn’t imagine the thrill I was about to experience. He pulled off my panties and slid his hands up the back of my nylon-covered legs right up to my ass. He then pulled my ass up in the air and spread my ass apart and began licking my opening. I clinched up initially.
“Are you okay?” Sam asked.
“Uh-huh,” I said in approval.
“It’s okay it is going to feel really good,” Sam said as he continued sticking his tongue in my hole and reaching around my waist and stroking my cock.
I couldn’t contain myself; it felt so good that I just continuously moaned louder and louder.
“Do you want more?” Sam asked
“Yes. Oh God Yes.” I said repeatedly.
He got up to his knees and with his wet finger penetrated my hole. It felt so good feeling it slide in and out of me.
“Are you ready?” Sam asked.
“mmmHmmm,” I mumbled.
And with that sound, he took his fingers out and the next sensation I felt was the tip of his cock pushing on my hole.
“UUUHHHH…..” I grunted.
“Nice and easy baby.” He said.
“OOOOHHH YEAH.” I said.
He continued to push the tip against my pussy waiting for the right moment. It wasn’t long before that moment came.
“AH… AH… AAHHH… OOOOOO…” I said as I could feel his cock slowly slide into my pussy.
As pushed himself all the way into me, I started to shake with excitement. The sensation was so intense; I looked to find myself fully erect and groaned in approval… wanting more.
“Oh God yes,” I screamed. “More…. More…. MORE.”
“You are so tight baby.” He said.
“OH YEAH… FUCK ME… FUCK ME… OOOOOO…” I begged.
I love your virgin ass.” He said.
“COME ON BABY… GIVE IT TO ME… UH… UH… OOOHH… YYYYEEEEAAAHHHH…. FUUUCCK MEEEE…” I said with glorious approval and pleasure.
The more I spoke the faster he went until he was close to cumming. He pulled out and I never hesitated. I rolled over and sat right in front of him facing his rock hard cock ready to explode.
Sam let out a hard groan and shot his load all over me. I don’t know why I did it, but I opened my mouth and caught his cum as it shot all the way to the back of my throat. I continued to lick his cock until he was completely empty. I then took his cock and rubbed the cum on my face back onto his dick and took it back into my mouth again.
Sam just smiled and looked at me and asked, “Did you enjoy that?”
I didn’t say anything I just fell onto his waist and hugged him. The rest of the evening we laid in bed together until the morning. I woke up to see him in the shower and just stared at him. When he was drying off he saw me staring at him. He came over to me and gave me a gentle kiss on the lips.
“I do need to get going,” Sam said.
“I know,” I replied.
Without saying another word, he finished getting dressed and I put on a bathrobe and walked him to the door. We kissed one final time and he walked away.
I never saw Sam again. I never thought my first one night stand would be with a man, but for the first time; I was so aroused without actually having an orgasm. I wanted more and couldn’t wait to do it again.